期刊
JOURNAL OF PHOTOCHEMISTRY AND PHOTOBIOLOGY A-CHEMISTRY
卷 259, 期 -, 页码 41-46出版社
ELSEVIER SCIENCE SA
DOI: 10.1016/j.jphotochem.2013.02.024
关键词
[2+2]-Cycloaddition; Photochemistry; Flow chemistry; Functional group tolerance; photo-conjugation
资金
- UHasselt doctoral funds
The [2 + 2] photocycloaddition between maleimide and various alkenes was optimized in a simple custom-made UV flow reactor. While complete maleimide conversion is only achieved with excesses of at least 10 eq. of alkene and reaction times of 12-24 h in batch, complete reactions with yields in the range >98% could be obtained in 5 min in the flow reactor under strictly equimolar conditions. Functional alkenes carrying allyl, alcohol, amine and ether moieties were successfully conjugated in good yields under optimized reaction conditions. As is demonstrated, the reaction gains in flow most characteristics of a high-efficient reaction, making the process highly valuable for upscaled synthesis of maleimide conjugates. (C) 2013 Elsevier B.V. All rights reserved.
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